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Winfield Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Winfield holiday rentals

Games room

1. Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV

Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
Woodbine
8.0 out of 10, Very good, (2 reviews)
"The stay was at a beautiful new home. Great host. Location close to Interstate 70. I had everything I needed. Took in the sights in DC via the Greenline Metro. I would definitely stay here again."
United States
Scott C.
The price is AU$212
includes taxes & fees
23 Sept - 24 Sept
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
1 bedroom, free WiFi, bed sheets

2. Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (36 reviews)
"Great location, clean place. "
United States
Warren B.
The price is AU$302
includes taxes & fees
22 Sept - 23 Sept
Cozy, dog-friendly, downtown
Smart TV

3. Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (9 reviews)
"This was a great property in an excellent location! Communication was great and the whole process was seamless. "
United States
nikki b.
The price is AU$315
includes taxes & fees
30 Sept - 1 Oct
Pet-friendly, heart of downtown
1 bedroom, iron/ironing board, WiFi, bed sheets

4. Newly Renovated Cozy Basement w/Private Entrance

Newly Renovated Cozy Basement w/Private Entrance
Reisterstown
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay for the night."
United States
Sheila K.
The price is AU$247
includes taxes & fees
1 Oct - 2 Oct
Newly Renovated Cozy Basement w/Private Entrance
Exterior detail

5. Huge 1br apt, baby-friendly, dogs, walkable downtown

Huge 1br apt, baby-friendly, dogs, walkable downtown
Downtown Frederick
10.0 out of 10, Exceptional, (12 reviews)
"Great location for a peaceful solo night away -- thanks!"
United States
Kristina S.
The price is AU$342
includes taxes & fees
1 Oct - 2 Oct
Huge 1br apt, baby-friendly, dogs, walkable downtown
Smart TV, music library

6. Downtown Frederick retreat with parking. Dog- and baby-friendly!

Downtown Frederick retreat with parking. Dog- and baby-friendly!
Frederick
9.8 out of 10, Exceptional, (7 reviews)
"This place looked exactly like the photos, very clean, super organized, and well designed. We were very comfortable during our stay and would stay here again."
United States
Dvorak A.
Downtown Frederick retreat with parking. Dog- and baby-friendly!
Iron/ironing board, free WiFi, bed sheets

7. The Whimsy Loft-Cozy Private Suite in Westminster on 4 acres

The Whimsy Loft-Cozy Private Suite in Westminster on 4 acres
Westminster
The price is AU$281
includes taxes & fees
15 Oct - 16 Oct
The Whimsy Loft-Cozy Private Suite in Westminster on 4 acres
Smart TV

8. Huge, Downtown, Walkable, Coffee, Breweries, Dogs

Huge, Downtown, Walkable, Coffee, Breweries, Dogs
Downtown Frederick
10.0 out of 10, Exceptional, (2 reviews)
"Very comfortable and convenient stay with responsive hosts. Great amenities for longer stays with the w/d. Will be back!"
United States
Dave T.
Huge, Downtown, Walkable, Coffee, Breweries, Dogs
Exterior

9. Rural & Historic Detour Escape w/ Horses On-Site!

Rural & Historic Detour Escape w/ Horses On-Site!
Detour
9.0 out of 10, Wonderful, (8 reviews)
"We had a great time. It is an older house but wonderful. It is in the country with lots of green fields surrounding it. The porch with the rockers was my favorite place to be when we weren’t site seeing, It was so peaceful. I would definitely stay here again."
United States
Charla H.
The price is AU$596
includes taxes & fees
22 Sept - 23 Sept
Rural & Historic Detour Escape w/ Horses On-Site!
Property grounds

10. Cozy Guesthouse in Woodstock, MD

Cozy Guesthouse in Woodstock, MD
Woodstock
2.0 out of 10, (1 review)
"We didn’t stay. We when arrived, instead of a room in the guest house, we were expected to stay in a tentlike structure. In addition, the bathroom facilities were outdoor showers and commodes that required a climb up a set of stairs. Luckily we were able to secure a room at another facility. The owner supposedly requested a refund for me but I haven’t heard whether this has been approved."
United States
Marie E M.
The price is AU$330
includes taxes & fees
1 Oct - 2 Oct
Cozy Guesthouse in Woodstock, MD
TV

11. Downtown Loft on Market Street-Great Location

Downtown Loft on Market Street-Great Location
Downtown Frederick
The price is AU$156
includes taxes & fees
28 Sept - 29 Sept
Downtown Loft on Market Street-Great Location
House (3 Bedrooms) | Interior

12. Rural & Historic Detour Escape w/ Horses On-site!

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
The price is AU$608
includes taxes & fees
22 Sept - 23 Sept
Rural & Historic Detour Escape w/ Horses On-site!
Interior

13. Private Sauna, Fireplace and Country Views

Private Sauna, Fireplace and Country Views
Mount Airy
10.0 out of 10, Exceptional, (4 reviews)
"The property is excellent! Beautiful and peaceful surroundings. It was clean warm and welcoming. It’s pet friendly though we didn’t travel with pets. Outstanding host!"
United States
David M.
The price is AU$450
includes taxes & fees
20 Sept - 21 Sept
Private Sauna, Fireplace and Country Views
Property grounds

14. Green Street Oasis – Walk to Downtown Westminster & McDaniel College

Green Street Oasis – Walk to Downtown Westminster & McDaniel College
Westminster
8.4 out of 10, Very good, (8 reviews)
"The stay was nice and as advertised. It was a little noisy at night with the split house and close neighbors, but it was a nice place. "
United States
Payson D.
The price is AU$641
includes taxes & fees
1 Oct - 2 Oct
Green Street Oasis – Walk to Downtown Westminster & McDaniel College
Coffee/tea maker, fridge, microwave, oven

15. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (22 reviews)
"It was a great place to relax, sleep and come home to after busy days in Frederick area. We would definitely stay here again!"
United States
Janice M.
The price is AU$675
includes taxes & fees
26 Sept - 27 Sept
Newly constructed 6 bedroom home
Interior

16. Luxury Serene 3 BR Family Home • Spacious Kitchen/Huge Yard • Quiet • Near Parks

Luxury Serene 3 BR Family Home • Spacious Kitchen/Huge Yard • Quiet • Near Parks
Milford Mill
Luxury Serene 3 BR Family Home • Spacious Kitchen/Huge Yard • Quiet • Near Parks
Exterior

17. New townhouse

New townhouse
Frederick
9.6 out of 10, Exceptional, (12 reviews)
"We had a great time. It was perfect for us. I would highly recommend it to others and would not hesitate to return there when back in the area. "
United States
Tereasa G.
The price is AU$666
includes taxes & fees
6 Oct - 7 Oct
New townhouse
Terrace/patio

18. DC Luxury Family Retreat in Forest—Spacious Full of Fun w/ Zipline Waterfall

DC Luxury Family Retreat in Forest—Spacious Full of Fun w/ Zipline Waterfall
Gaithersburg
10.0 out of 10, Exceptional, (3 reviews)
"Had a great stay home was amazing "
United States
Darinda h.
The price is AU$1,211
includes taxes & fees
19 Sept - 20 Sept
DC Luxury Family Retreat in Forest—Spacious Full of Fun w/ Zipline Waterfall
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winfield Hotel Reviews

Turf Valley Resort

Turf Valley Resort

10/10 Excellent
"Beautifully appointed resort with updated rooms, including a huge bathroom with jacuzzi tub & large walk - in shower. Lovely view of the well maintained golf course from balcony. Extremely polite & helpful staff. Dining experience for breakfast was good. Only negative would be the shower floor is smooth tile & very slippery!. Also a noticeable amount of flies in the bar/restaurant area most likely due to adjacent outdoor patio seating. Overall would still give a five star rating."
Mike 1-night trip
Posted 9 hours ago
Turf Valley Resort

Find out more about Winfield

Everything you need to know about Winfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winfield holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winfield holiday rentals we have selected for you start as low as AU$302 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winfield rentals

At Expedia, we put the best Winfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Winfield?

Yes, there are holiday rentals close to the most popular sights in Winfield, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winfield has to offer?

Rural & Historic Detour Escape w/ Horses On-Site!: This holiday home rental outside of Winfield offers a patio, a selection of books and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Winfield?

Explore the area and family-friendly sights such as Adventure Park USA, or get out into nature at a spot like Union Mills Homestead Park. Old Westminster Winery and Sykesville Town Hall are a couple of places you'll find in the wider area.

What’s a holiday rental in Winfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winfield. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family trips.